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$59+ Cheap flights from Midway (MDW) to Oklahoma

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OKC
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Midway to Oklahoma

Keep the following information in mind while searching for Midway to Oklahoma flight deals. Data was last updated September 15, 2025.

Round-trip from

$100
(Kiwi.com)

One-way from

$59
(Southwest)

Popular in

January

Cheapest in

July

Average price

$340

Good round-trip deal

$285 or less

Good one-way deal

$114 or less
From Chicago Midway to Oklahoma
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One-way flight from Chicago Midway to Oklahoma
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Highest demand for flights based on searches. 7% potential increase in price ($28 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago Midway to Oklahoma.
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Price to beat on a one-way flight from Chicago Midway to Oklahoma.
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Find flight deals from Midway to Oklahoma

Cheapest flights from Midway to Oklahoma
Explore the most affordable flight options available from Midway to Oklahoma. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/175:10 amMDW - DFW
Nonstop2h 35mFrontier
Mon 10/209:01 pmDFW - MDW
Nonstop2h 19mFrontier
Deal found 9/14$100
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/175:10 amMDW - DFW
Nonstop2h 35mFrontier
Sun 10/269:01 pmDFW - MDW
Nonstop2h 19mFrontier
Deal found 9/13$101
This CheapOair deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/235:20 pmMDW - DFW
Nonstop2h 41mFrontier
Sun 10/269:01 pmDFW - MDW
Nonstop2h 19mFrontier
Deal found 9/13$102
This Priceline deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/78:55 amMDW - DFW
Nonstop2h 33mFrontier
Mon 11/173:39 pmDFW - MDW
Nonstop2h 20mFrontier
Deal found 9/13$103
This Cheapflightsfares deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/39:47 pmMDW - DFW
Nonstop2h 34mFrontier
Sun 10/57:00 amDFW - MDW
Nonstop2h 23mFrontier
Deal found 9/13$104
This Cheapflightsfares deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/95:20 pmMDW - DFW
Nonstop2h 41mFrontier
Tue 10/149:01 pmDFW - MDW
Nonstop2h 19mFrontier
Deal found 9/13$105
This Frontier deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/115:20 pmMDW - DFW
Nonstop2h 41mFrontier
Tue 10/149:01 pmDFW - MDW
Nonstop2h 19mFrontier
Deal found 9/14$106
This Priceline deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/309:43 pmMDW - DFW
Nonstop2h 38mFrontier
Fri 10/312:57 pmDFW - MDW
Nonstop2h 18mFrontier
Deal found 9/14$107
This CheapOair deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/210:13 amMDW - DFW
Nonstop2h 38mFrontier
Sat 10/48:00 amDFW - MDW
Nonstop2h 28mFrontier
Deal found 9/13$108
This Frontier deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/205:10 amMDW - DFW
Nonstop2h 35mFrontier
Sun 10/269:01 pmDFW - MDW
Nonstop2h 19mFrontier
Deal found 9/12$110
This CheapOair deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/39:47 pmMDW - DFW
Nonstop2h 34mFrontier
Mon 10/65:40 amDFW - MDW
1 stop10h 45mFrontier
Deal found 9/13$111
This Frontier deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/34:48 pmMDW - OKC
1 stop7h 06mFrontier
Mon 10/66:05 amOKC - MDW
1 stop9h 48mFrontier
Deal found 9/14$150

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Oklahoma that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Oklahoma that are best for you.

Fly from

Midway

Fly to

Oklahoma

Route

Depart

Return

Price

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Thu 11/6

9:34 pm-12:12 am

Nonstop2h 38m

Dallas/Fort Worth

Mon 11/10

2:57 pm-5:15 pm

Nonstop2h 18m

$103

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Thu 10/23

5:20 pm-8:01 pm

Nonstop2h 41m

Dallas/Fort Worth

Sun 10/26

5:14 am-12:36 am

1 stop19h 22m

$112

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Tue 10/7

5:20 pm-8:01 pm

Nonstop2h 41m

Dallas/Fort Worth

Sat 10/11

9:01 pm-11:20 pm

Nonstop2h 19m

$114

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Thu 10/16

6:24 pm-12:24 am

1 stop6h 00m

Dallas/Fort Worth

Tue 10/21

9:01 pm-11:20 pm

Nonstop2h 19m

$116

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Fri 10/17

5:10 am-7:45 am

Nonstop2h 35m

Dallas/Fort Worth

Thu 11/6

1:51 pm-10:03 pm

1 stop8h 12m

$121

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Fri 10/3

9:47 pm-12:21 am

Nonstop2h 34m

Dallas/Fort Worth

Sun 10/5

7:00 am-9:23 am

Nonstop2h 23m

$122

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Fri 10/17

6:24 pm-12:24 am

1 stop6h 00m

Dallas/Fort Worth

Mon 10/20

9:01 pm-11:20 pm

Nonstop2h 19m

$129

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Fri 11/7

1:37 pm-10:13 pm

1 stop8h 36m

Dallas/Fort Worth

Sun 11/9

5:35 am-11:30 am

1 stop5h 55m

$146

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Fri 9/19

7:15 am-9:46 am

Nonstop2h 31m

Dallas/Fort Worth

Sun 9/21

7:00 am-9:23 am

Nonstop2h 23m

$148

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Fri 10/10

6:24 pm-12:24 am

1 stop6h 00m

Dallas/Fort Worth

Thu 10/16

1:51 pm-8:21 pm

1 stop6h 30m

$150

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 60 results
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Best time to book a flight from Midway to Oklahoma

Have a flexible travel schedule? Discover the best time to fly to Oklahoma from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Oklahoma

What is the cheapest month to book a flight from Chicago Midway Airport to Oklahoma?

Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Oklahoma (average of $334). Flying from Chicago Midway Airport to Oklahoma in June is currently the most expensive (average of $401). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MDW to OK?

Find hourly flight availability from Midway to Oklahoma. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Oklahoma as you normally would.

Reviews of airlines servicing Oklahoma

Get insights into the airlines that provide service to Oklahoma. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Oklahoma. Reviews last updated September 15, 2025.
Peruse reviews from past customers who have flown with Southwest from Chicago Midway Airport to Oklahoma to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,245 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Midway to Oklahoma. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago Midway Airport to Oklahoma?

    Departing from Chicago Midway Airport to Oklahoma will take you 2h. The distance between Chicago Midway Airport and Oklahoma is about 690 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most popular routes from Chicago Midway Airport to Oklahoma?

    While some choose either Chicago Midway - Oklahoma City Will Rogers World or Chicago Midway - Fayetteville Northwest Arkansas, Chicago Midway - Dallas/Fort Worth is the most popular route from Chicago Midway Airport to Oklahoma.

  • What are the cheapest flights from Chicago Midway Airport to Oklahoma?

    The cheapest flight price from Chicago Midway Airport to Oklahoma is $114. On average you can expect to pay $334. The most popular route, (Chicago Midway - Dallas/Fort Worth), can usually be booked for $74.

  • Can I find deals for flights from Midway to Oklahoma that include hotel bookings?

    Yes. In addition to deals on Midway to Oklahoma flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Oklahoma?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Oklahoma.

  • Can I find deals for business class flights from Midway to Oklahoma?

    Yes. Cheapflights offers flight deals from Midway to Oklahoma by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Oklahoma?

    Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Oklahoma (average of $334). Flying from Chicago Midway Airport to Oklahoma in June is currently the most expensive (average of $401). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Midway to Oklahoma

See prices for flight routes from nearby airports that may be better suited for you.
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Midway to Seattle flights

Top airline flying from Midway to Oklahoma

Discover the top airline that operate flights from Midway to Oklahoma. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$131Average$350FlexibilityNo cancel feeOn-time63%

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